Heterocyclic compound and organic light-emitting diode including the same

ABSTRACT

A heterocyclic compound is represented by Formula 1. The heterocyclic compound may be used in an organic layer of an organic light-emitting diode. An organic light-emitting diode includes a first electrode, a second electrode and an organic layer, and the organic layer includes the heterocyclic compound represented by Formula 1. The organic light-emitting diode may be used in a flat panel display device, in which the first electrode of the organic light-emitting diode may be electrically connected to a source or drain electrode of a thin film transistor.

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority to and the benefit of Korean PatentApplication No. 10-2013-0019374, filed on Feb. 22, 2013 in the KoreanIntellectual Property Office, the entire content of which isincorporated herein by reference.

BACKGROUND

1. Technical Field

The present invention relates to a heterocyclic compound and an organiclight-emitting diode including the same.

2. Description of the Related Art

Organic light-emitting diodes (OLEDs) are self-emitting diodes havingadvantages such as wide viewing angles, good contrast, quick responsespeeds, high brightness, and good driving voltages. Also, OLEDs canprovide multicolored images.

A typical diode has a structure including a substrate, an anode formedon the substrate, and a hole transport layer (HTL), an emission layer(EML), an electron transport layer (ETL), and a cathode sequentiallystacked on the substrate. The HTL, the EML, and the ETL are organic thinfilms formed of organic compounds.

An operating principle of an OLED having the above-described structureis as follows. When a voltage is applied between the anode and thecathode, holes injected from the anode move to the EML via the HTL, andelectrons injected from the cathode move to the EML via the ETL. Theholes and electrons (carriers) recombine in the EML to generateexcitons. When the excitons drop from an excited state to a groundstate, light is emitted.

While conventional OLEDs may use monomolecular materials, there isongoing demand for a material having improved electrical stability, highcharge-transferring and light-emitting abilities, good emissioncapability, a high glass transition temperature, and that is capable ofpreventing crystallization.

SUMMARY

Embodiments of the present invention provide a heterocyclic compound andan organic light-emitting diode (OLED) including the same. The compoundhas good electrical properties, high charge-transferring abilities, andhigh light-emitting ability. The compound, which is a material having ahigh glass transition temperature and that is capable of preventingcrystallization, can be effectively used as an electron-transportingmaterial or an electron-injecting material suitable for fluorescent andphosphorescent diodes of any color, e.g., red, green, blue, or white.Therefore, a light-emitting diode having high efficiency, low drivingvoltage, high luminance, and a long lifetime may be manufactured usingthe compound.

According to an aspect of the present invention, a heterocyclic compoundis represented by Formula 1 below:

In Formula 1, A and B may each independently be a single bond or abivalent linker that is a substituted or unsubstituted C₆-C₃₀ arylenegroup, a substituted or unsubstituted C₂-C₃₀ heteroarylene group, or asubstituted or unsubstituted C₆-C₃₀ condensed polycyclic group.

R₁, R₂, and R₃ may each independently be a hydrogen atom, a deuteriumatom, a substituted or unsubstituted C₁-C₆₀ alkyl group, a substitutedor unsubstituted C₃-C₆₀ cycloalkyl group, a substituted or unsubstitutedC₆-C₆₀ aryl group, a substituted or unsubstituted C₂-C₆₀ heteroarylgroup, a substituted or unsubstituted C₆-C₃₀ condensed polycyclic group,a fluoro group, or a cyano group.

Ar₁ and Ar₂ may each independently be a substituted or unsubstitutedC₆-C₃₀ aryl group, a substituted or unsubstituted C₂-C₃₀ heteroarylgroup, or a substituted or unsubstituted C₆-C₃₀ condensed polycyclicgroup.

According to another aspect of the present invention, an OLED includes afirst electrode, a second electrode, and an organic layer between thefirst electrode and the second electrode. The organic layer includes thecompound of Formula 1 above.

According to another aspect of the present invention, the OLED isprovided in a flat panel display device, and the first electrode on thesubstrate of the OLED is electrically connected to a source electrode ora drain electrode of a thin-film transistor (TFT).

BRIEF DESCRIPTION OF THE DRAWING

The above and other features and advantages of the present inventionwill become more apparent by reference to the following detaileddescription when considered in conjunction with the attached drawing inwhich:

FIG. 1 is a schematic view of a structure of an organic light-emittingdiode (OLED) according to an embodiment of the present invention.

DETAILED DESCRIPTION

As used herein, the term “and/or” includes any and all combinations ofone or more of the associated listed items. Expressions such as “atleast one of,” when preceding a list of elements, modify the entire listof elements and do not modify the individual elements of the list.

According to an aspect of the present invention, a heterocyclic compoundis represented by Formula 1 below:

In Formula 1, A and B may each independently be a single bond or abivalent linker that is a substituted or unsubstituted C₆-C₃₀ arylenegroup, a substituted or unsubstituted C₂-C₃₀ heteroarylene group, or asubstituted or unsubstituted C₆-C₃₀ condensed polycyclic group.

R₁, R₂, and R₃ may each independently be a hydrogen atom, a deuteriumatom, a substituted or unsubstituted C₁-C₆₀ alkyl group, a substitutedor unsubstituted C₃-C₆₀ cycloalkyl group, a substituted or unsubstitutedC₆-C₆₀ aryl group, a substituted or unsubstituted C₂-C₆₀ heteroarylgroup, a substituted or unsubstituted C₆-C₃₀ condensed polycyclic group,a fluoro group, or a cyano group.

Ar₁ and Ar₂ may each independently be a substituted or unsubstitutedC₆-C₃₀ aryl group, a substituted or unsubstituted C₂-C₃₀ heteroarylgroup, or a substituted or unsubstituted C₆-C₃₀ condensed polycyclicgroup.

According to embodiments of the present invention, the compound ofFormula 1 may function as a light-emitting material of the OLED. Forexample, the compound of Formula 1 may be effectively used as a bluefluorescent dopant.

Also, the compound of Formula 1 above has a high glass transitiontemperature (Tg) or melting point due to the introduction of theheterocyclic group. Therefore, the compound of Formula 1 above increasesthe thermal resistance of the OLED and the high-temperature resistanceagainst Joule's heat that is generated in the organic layer, betweenorganic layers, or between the organic layer and a metal electrode. TheOLED manufactured using the heterocyclic compound has improvedadvantages such as high durability during storage or operation.

In some embodiments, the compound of Formula 1 above may be representedby Formula 2 or Formula 3 below:

In Formulae 2 and 3, the definitions of the substituents are the same asin Formula 1 above.

In some embodiments, Ar₁ and Ar₂ in Formula 1 above may combine witheach other or adjacent substituents to form a ring.

The substituents in the compound of Formula 1 above will be described inmore detail.

In some embodiments, R₁ in Formula 1 above may be a substituted orunsubstituted C₁-C₃₀ alkyl group, or a compound represented by Formula2a or Formula 2b below:

In Formulas 2a and 2b, Z₁ may be a hydrogen atom, a deuterium atom, ahalogen atom, —CN, a substituted or unsubstituted C₁-C₂₀ alkyl group, asubstituted or unsubstituted C₆-C₂₀ aryl group, or a substituted orunsubstituted C₆-C₂₀ heteroaryl group.

Y₁ may be CH or N.

p may be an integer from 1 to 6.

* may be a binding site.

In some other embodiments, R₂ and R₃ in Formula 1 above may eachindependently be a hydrogen atom, a deuterium atom, a substituted orunsubstituted C₁-C₃₀ alkyl group, or a compound represented by Formula3a below:

In Formula 3a, Z₁ may be a hydrogen atom, a deuterium atom, a halogenatom, —CN, a substituted or unsubstituted C₁-C₂₀ alkyl group, asubstituted or unsubstituted C₆-C₂₀ aryl group, or a substituted orunsubstituted C₆-C₂₀ heteroaryl group.

p may be an integer from 1 to 5.

* may be a binding site.

In some other embodiments, Ar₁ and Ar₂ in Formula 1 may eachindependently be one of the compounds represented by Formulas 4a to 4dbelow:

In Formulas 4a to 4d, Z₁ may be a hydrogen atom a deuterium atom, ahalogen atom, —CN, a substituted or unsubstituted C₁-C₂₀ alkyl group, asubstituted or unsubstituted C₆-C₂₀ aryl group, or a substituted orunsubstituted C₆-C₂₀ heteroaryl group.

Y₁ may be CH or N.

Q₁ may be a linker represented by —C(R₃₀)(R₃₁)—, —S—, or —O—.

R₃₀ and R₃₁ may each independently be a hydrogen atom, a deuterium atom,a substituted or unsubstituted C₁-C₂₀ alkyl group, a substituted orunsubstituted C₅-C₂₀ aryl group, or a substituted or unsubstitutedC₆-C₂₀ condensed polycyclic group.

p may be an integer from 1 to 9.

* may be a binding site.

In some other embodiments, A and B in Formula 1 above may eachindependently be a single bond, one of the compounds represented byFormulas 5a to 5e below, or a linker connecting at least two of thecompounds represented by Formulas 5a to 5e below.

In Formulas 5a to 5e, Y₁ may be CH or N.

Q₂ may be a linker represented by —C(R₃₀)(R₃₁)—, —S—, or —O—.

R₃₀ and R₃₁ may each independently be a hydrogen atom, a deuterium atom,a substituted or unsubstituted C₁-C₂₀ alkyl group, a substituted orunsubstituted C₅-C₂₀ aryl group, or a substituted or unsubstitutedC₆-C₂₀ condensed polycyclic group.

* may be a binding site.

Hereinafter, the definition of representative substituents used hereinwill be described. However, the numbers of carbons in a substituent arenon-limited, and thus, the substituent characteristics are not limited.The substituents not defined herein are defined as substituentsgenerally known to one of ordinary skill in the art.

The unsubstituted C₁-C₆₀ alkyl group, as used herein, refers to a linearor branched alkyl group. Non-limiting examples of the unsubstitutedC₁-C₆₀ alkyl group include a methyl group, an ethyl group, a propylgroup, an iso-butyl group, a sec-butyl group, a pentyl group, aniso-amyl group, a hexyl group, a heptyl group, an octyl group, a nonanylgroup, and a dodecyl group. The substituted C₁-C₆₀ alkyl group refers tothe substitution of at least one hydrogen atom of the unsubstitutedC₁-C₆₀ alkyl group with a deuterium atom, a halogen atom, a hydroxylgroup, a nitro group, a cyano group, an amino group, an amidino group, ahydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a C₂-C₁₀ alkenyl group, aC₂-C₁₀ alkynyl group, a C₆-C₁₆ aryl group, or a C₄-C₁₆ heteroaryl group.

The unsubstituted C₂-C₆₀ alkenyl group refers to an unsubstitutedalkenyl group having at least one carbon-carbon double bond in thecenter or at a terminal end thereof. Non-limiting examples of theunsubstituted C₂-C₆₀ alkenyl group include an ethenyl group, a propenylgroup, a butenyl group, and the like. The substituted C₂-C₆₀ alkenylgroup refers to the substitution of at least one hydrogen atom of theunsubstituted alkenyl group with the substituents described above inconnection with the substituted alkyl group.

The unsubstituted C₂-C₆₀ alkynyl group refers to an unsubstitutedalkynyl group having at least one carbon-carbon triple bond in thecenter or at a terminal end thereof. Non-limiting examples of theunsubstituted C₂-C₆₀ alkynyl group include acetylene, propylene,phenylacetylene, naphthylacetylene, isopropylacetylene,t-butylacetylene, diphenylacetylene, and the like. The substitutedC₂-C₆₀ alkynyl group refers to the substitution of at least one hydrogenatom of the unsubstituted C₂-C₆₀ alkynyl group with the substituentsdescribed above in connection with the substituted alkyl group.

The unsubstituted C₃-C₆₀ cycloalkyl group refers to an alkyl grouphaving a C₃-C₆₀ ring. The substituted C₃-C₆₀ cycloalkyl group refers tothe substitution of at least one hydrogen atom of the C₃-C₆₀ cycloalkylgroup with the substituents described above in connection with theC₁-C₆₀ alkyl group.

The unsubstituted C₁-C₆₀ alkoxy group is represented by —OA where A isan unsubstituted C₁-C₆₀ alkyl group, as described above. Non-limitingexamples of the unsubstituted C₁-C₆₀ alkoxy group include a methoxygroup, an ethoxy group, a propoxy group, an isopropyloxy group, a butoxygroup, a pentoxy group, and the like. The substituted C₁-C₆₀ alkoxygroup refers to the substitution of at least one hydrogen atom of theunsubstituted alkoxy group with the substituents described above inconnection with the substituted alkyl group.

The unsubstituted C₆-C₆₀ aryl group refers to a carbocyclic aromaticsystem including at least one ring. When the unsubstituted C₆-C₆₀ arylgroup has two or more rings, the rings may be fused to each other orlinked to each other by a single bond. For example, the ‘aryl’ group mayinclude an aromatic system such as phenyl, naphthyl, and anthracenyl.Also, the substituted C₆-C₆₀ aryl group refers to the substitution of atleast one hydrogen atom of the aryl group with the substituentsdescribed above in connection with the C₁-C₆₀ alkyl group.

Non-limiting examples of the substituted or unsubstituted C₆-C₆₀ arylgroup include a phenyl group, a C₁-C₁₀ alkylphenyl group (i.e., anethylphenyl group), a biphenyl group, a C₁-C₁₀ alkylbiphenyl group, aC₁-C₁₀ alkoxybiphenyl group, an o-, m-, or p-toryl group, an o-, m-, orp-cumenyl group, a mesityl group, a phenoxyphenyl group, a(α,α-dimethylbenzene)phenyl group, a (N,N′-dimethyl)aminophenyl group, a(N,N′-diphenyl)aminophenyl group, a pentalenyl group, an indenyl group,a naphthyl group, a C₁-C₁₀ alkylnaphthyl group (i.e., a methylnaphthylgroup), a C₁-C₁₀ alkoxynaphthyl group (i.e., a methoxynaphthyl group),an anthracenyl group, an azulenyl group, a heptalenyl group, anacenaphthalenyl group, a phenalenyl group, a fluorenyl group, ananthraquinolyl group, a methylanthryl group, a phenanthryl group, atriphenylene group, a pyrenyl group, a chrysenyl group, anethyl-chrysenyl group, a picenyl group, a perylenyl group, a pentaphenylgroup, a pentacenyl group, a tetraphenylenyl group, a hexaphenyl group,a hexacenyl group, a rubicenyl group, a coronenyl group, atrinaphthalenyl group, a heptaphenyl group, a heptacenyl group, apyranthrenyl group, an ovalenyl group, and the like.

The unsubstituted C₂-C₆₀ heteroaryl group, as used herein, refers to anaryl group including one, two, three, or four hetero atoms selected fromN, O, P, or S. When the unsubstituted C₂-C₆₀ heteroaryl group has two ormore rings, the rings may be fused to each other or linked to each otherby a single bond. Non-limiting examples of the unsubstituted C₄-C₆₀heteroaryl group include a pyrazolyl group, an imidazolyl group, anoxazolyl group, a thiazolyl group, a triazolyl group, a tetrazolylgroup, an oxadiazolyl group, a pyridinyl group, a pyridazinyl group, apyrimidinyl group, a triazinyl group, a carbazolyl group, an indolylgroup, a quinolyl group, an isoquinolyl group, and a dibenzothiophenegroup, and the like. In addition, the substituted C₂-C₆₀ heteroarylgroup refers to the substitution of at least one hydrogen atom of theheteroaryl group with the substituents described above in connectionwith the unsubstituted C₁-C₆₀ alkyl group.

The unsubstituted C₅-C₆₀ aryloxy group is a group represented by —OA₁,where A₁ is a C₅-C₆₀ aryl group. Non-limiting examples of the aryloxygroup include a phenoxy group, and the like. The substituted C₅-C₆₀aryloxy group refers to the substitution of at least one hydrogen atomof the aryloxy group with the substituents described above in connectionwith the unsubstituted C₁-C₆₀ alkyl group.

The unsubstituted C₅-C₆₀ arylthio group is a group represented by —SA₁,where A₁ is a C₅-C₆₀ aryl group. Non-limiting examples of the arylthiogroup include a benzenethio group, a naphthylthio group, and the like.The substituted C₅-C₆₀ arylthio group refers to the substitution of atleast one hydrogen atom of the arylthio group with the substituentsdescribed above in connection with the unsubstituted C₁-C₆₀ alkyl group.

The unsubstituted C₆-C₆₀ condensed polycyclic group, as used herein,refers to either: i) a substituent including at least two rings in whichat least one aromatic ring and/or at least one non-aromatic ring arefused to each other; or ii) a substituent having an unsaturated groupwithin a ring, but that is unable to form a conjugated structure.Therefore, the unsubstituted C₆-C₆₀ condensed polycyclic group isdistinct from the aryl group or the heteroaryl group as it has anon-aromatic component.

Non-limiting examples of the compound of Formula 1 include the followingcompounds represented by Formulas 1 to 137 below:

According to another aspect of the present invention, an OLED includes afirst electrode, a second electrode, and an organic layer between thefirst electrode and the second electrode. The organic layer includes thecompound of Formula 1 above.

The organic layer may include at least one layer selected from a holeinjection layer (HIL), a hole transport layer (HTL), a functional layerhaving both hole injection and hole transport capabilities (hereinafter,referred as a “H-functional layer”), a buffer layer, an electronblocking layer (EBL), an emission layer (EML), a hole blocking layer(HBL), an electron transport layer (ETL), an electron injection layer(EIL), or a functional layer having both electron injection and electrontransport capabilities (hereinafter, referred as an “E-functionallayer”).

The organic layer may be used as an EML, for example a blue EML.

In some embodiments, the OLED may include an EIL, an ETL, an EML, a HIL,a HTL, or a H-functional layer having both hole injection and holetransport capabilities, and the EML may include the compound of Formula1 above, and an anthracene-based compound, an arylamine-based compound,or a styryl-based compound.

In some other embodiments, the OLED may include an EIL, an ETL, an EML,a HIL, a HTL, or a H-functional layer having both hole injection andhole transport capabilities, and at least one of a red EML, a green EML,a blue EML, or a white EML of the EML may include a phosphorescentcompound. The EML may include a compound according to an embodiment ofthe present invention, and may further include a charge-generatingmaterial in addition to the above-mentioned compound. Thecharge-generating material may be a p-dopant, and the p-dopant may be aquinone derivative, a metal oxide, or a cyano group-containing compound.

In some other embodiments, the organic layer may include an ETL, and theETL may include an electron-transporting organic compound and a metalcomplex. The metal complex may be a lithium (Li) complex.

The term “organic layer,” as used herein, refers to a single layerand/or a multi-layered structure disposed between the first electrodeand the second electrode of the OLED.

FIG. 1 is a schematic view of a structure of an OLED according to anembodiment of the present invention. Hereinafter, a structure andmanufacturing method of an OLED according to an embodiment of thepresent invention will be described with reference to FIG. 1.

The substrate (not illustrated) may be any substrate generally used inOLEDs, e.g., a glass substrate or transparent plastic substrate havingmechanical strength, thermal stability, transparency, surfacesmoothness, ease of handling, and water resistance.

The first electrode may be formed by depositing or sputtering a firstelectrode material on the substrate. When the first electrode is ananode, the first electrode material may be selected from materials witha high work function to enable ease of hole injection. The firstelectrode may be a reflective electrode or a transmission electrode. Thefirst electrode material may be a transparent material with highconductivity, and examples thereof include indium tin oxide (ITO),indium zinc oxide (IZO), tin oxide (SnO₂), and zinc oxide (ZnO). Whenmagnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca),magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), or the like is used,the first electrode may be a reflective electrode.

The first electrode may have a single-layer structure or a multi-layeredstructure including at least two layers. For example, the firstelectrode may have a three-layered structure of ITO/Ag/ITO, but is notlimited thereto.

The organic layer may be disposed on the first electrode.

The organic layer may include a HIL, a HTL, a buffer layer (notillustrated), an EML, an ETL, and/or an EIL.

The HIL may be formed on the first electrode by various methods such asvacuum deposition, spin coating, casting, and Langmuir-Blodgett (LB)deposition. When the HIL is formed using vacuum deposition, the vacuumdeposition conditions may vary depending on the compound used to formthe HIL, and the desired structural and thermal properties of the HIL tobe formed. For example, the vacuum deposition may be performed at atemperature of about 100° C. to about 500° C., a pressure of about 10⁻⁸torr to about 10⁻³ torr, and a deposition rate of about 0.01 Å/sec toabout 100 Å/sec. However, the deposition conditions are not limitedthereto.

When the HIL is formed using spin coating, the coating conditions mayvary depending on the compound used to form the HIL, and the desiredstructural and thermal properties of the HIL to be formed. For example,the coating rate may be about 2,000 rpm to about 5,000 rpm, and thetemperature at which heat treatment is performed to remove solvent aftercoating may be about 80° C. to about 200° C. However, the coatingconditions are not limited thereto.

As a material for the HIL, any hole-injecting material may be used, forexample,N,N′-diphenyl-N,N′-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4′-diamine(DNTPD), a phthalocyanine compound such as copper phthalocyanine,4,4′,4″-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA),N,N′-di(1-naphthyl)-N,N′-diphenylbenzidine (NPB), TDATA, 2-TNATA,polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS),polyaniline/camphor sulfonicacid (Pani/CSA), orpolyaniline/poly(4-styrenesulfonate) (PANI/PSS). However, thehole-injecting material is not limited thereto.

A thickness of the HIL may be about 100 Å to about 10,000 Å, forexample, about 100 Å to about 1000 Å. When the thickness of the HIL iswithin the above ranges, the HIL may have satisfactory hole injectioncharacteristics without a substantial increase in driving voltage.

Then, the HTL may be formed on the HIL by vacuum deposition, spincoating, casting, LB deposition, or the like. When the HTL is formedusing vacuum deposition or spin coating, the deposition or coatingconditions may be similar to those described above for formation of theHIL. However, the deposition and coating conditions may vary dependingon the compound used to form the HTL.

As a material for the HTL, any hole-transporting material may be used,for example, a carbazole derivative such as N-phenylcarbazole orpolyvinylcarbazole,N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1-biphenyl]-4,4′-diamine(TPD), 4,4′,4″-tris(N-carbazolyl)triphenylamine) (TCTA), andN,N′-di(1-naphthyl)-N,N′-diphenylbenzidine (NPB). However, thehole-transporting material is not limited thereto.

A thickness of the HTL may be about 50 Å to about 2,000 Å, for example,about 100 Å to about 1,500 Å. When the thickness of the HTL is withinthe above ranges, the HTL may have satisfactory hole transportcharacteristics without a substantial increase in driving voltage.

The H-functional layer (i.e., the functional layer having both holeinjection and hole transport capabilities) may include one or morematerials selected from the above-described materials for the HIL andthe HTL. A thickness of the H-functional layer may be about 500 Å toabout 10,000 Å, for example, about 100 Å to about 1,000 Å. When thethickness of the H-functional layer is within the above ranges, theH-functional layer may have satisfactory hole injection and transportcharacteristics without a substantial increase in driving voltage.

In some embodiments, at least one of the HIL, the HTL, and theH-functional layer may include at least one of the following compoundsrepresented by Formulas 300 and 350.

Ar₁₁, Ar₁₂, Ar₂₁, and Ar₂₂ in Formulas 300 and 350 may eachindependently be a substituted or unsubstituted C₅-C₆₀ arylene group.

e and f in Formula 300 may each independently be an integer from 0 to 5,for example, 0, 1, or 2. In some embodiments, e may be 1 and f may be 0,but the present invention is not limited thereto.

R₅₁ to R₅₈, R₆₁ to R₆₉ and R₇₁, and R₇₂ in Formulas 300 and 350 may eachindependently be a hydrogen atom, a deuterium atom, a halogen atom, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₆₀ cycloalkylgroup, a substituted or unsubstituted C₅-C₆₀ aryl group, a substitutedor unsubstituted C₅-C₆₀ aryloxy group, or a substituted or unsubstitutedC₅-C₆₀ arylthio group. For example, R₅₁ to R₅₈, R₆₁ to R₆₉ and R₇₁, andR₇₂ may each independently be:

i) a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group,a cyano group, a nitro group, an amino group, an amidino group, ahydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₁₀ alkyl group (e.g., a methyl group, an ethyl group, a propylgroup, a butyl group, a pentyl group, a hexyl group, or the like), aC₁-C₁₀ alkoxy group (e.g., a methoxy group, an ethoxy group, a propoxygroup, a butoxy group, a pentoxy group, or the like); or

ii) a C₁-C₁₀ alkyl group or a C₁-C₁₀ alkoxy group substituted with atleast one of a deuterium atom, a halogen atom, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazine, ahydrazone, a carboxyl group or a salt thereof, a sulfonic acid group ora salt thereof, or a phosphoric acid group or a salt thereof; or

iii) a phenyl group, a naphthyl group, an anthryl group, a fluorenylgroup, or a pyrenyl group; or

iv) a phenyl group, a naphthyl group, an anthryl group, a fluorenylgroup, or a pyrenyl group substituted with at least one of a deuteriumatom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine, a hydrazone, a carboxylgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₁₀ alkyl group, or aC₁-C₁₀ alkoxy group.

However, R₅₁ to R₅₈, R₆₁ to R₆₉ and R₇₁, and R₇₂ are not limited to theabove.

R₅₉ in Formula 300 may be a phenyl group, a naphthyl group, an anthrylgroup, a biphenyl group, or a pyridyl group; or

a phenyl group, a naphthyl group, an anthryl group, a biphenyl group, ora pyridyl group substituted with at least one of a deuterium atom, ahalogen atom, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine, a hydrazone, a carboxyl group or asalt thereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a substituted or unsubstituted C₁-C₂₀ alkylgroup, or a substituted or unsubstituted C₁-C₂₀ alkoxy group.

In some embodiments, the compound of Formula 300 may be represented by300A below, but the compound is not limited thereto.

R₅₁, R₆₂, R₆₁, and R₅₉ in Formula 300A are as described above.

For example, at least one of the HIL, HTL, and the H-functional layermay include at least one of the following Compounds 301 to 320, but theHIL, HTL, and the H-functional layer are not limited thereto:

In addition to hole-injecting materials, hole-transporting materials,and/or H-functional materials having both hole injection and holetransport capabilities, at least one of the HIL, HTL, and theH-functional layer may further include a charge-generating material toimprove the conductivity of the film.

The charge-generating material may be, for example, a p-dopant. Thep-dopant may be one of a quinone derivative, a metal oxide, or acompound with a cyano group, but is not limited thereto. Non-limitingexamples of the p-dopant include quinone derivatives such astetracyanoquinodimethane (TCNQ) and2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ); metaloxides such as a tungsten oxide and a molybdenum oxide; and cyanogroup-containing compounds such as Compound 200 below.

When the HIL, the HTL, or the H-functional layer further includes thecharge-generating material, the charge-generating material may behomogeneously dispersed or non-homogeneously distributed in the layer.

A buffer layer may be disposed between the EML and at least one of theHIL, HTL, and the H-functional layer. The buffer layer may compensatefor an optical resonance distance of light according to a wavelength ofthe light emitted from the EML, and thus may increase efficiency. Thebuffer layer may include any hole injecting material or holetransporting material generally used in OLEDs. In some otherembodiments, the buffer layer may include the same material as one ofthe materials included in the HIL, the HTL, or the H-functional layerthat underlie the buffer layer.

Then, the EML may be formed on the HIL, the H-functional layer, or thebuffer layer by vacuum deposition, spin coating, casting, LB deposition,or the like. When the EML is formed using vacuum deposition or spincoating, the deposition or coating conditions may be similar to thosedescribed above for formation of the HIL, although the conditions fordeposition or coating may vary depending on the material used to formthe EML.

The EML may include the compound of Formula 1 as described above. Forexample, the compound of Formula 1 may be used as a host or a dopant. Inaddition to the compound of Formula 1, the EML may be formed using avariety of light-emitting materials, for example, a host and a dopant.In regard to the dopant, both a fluorescent dopant and a phosphorescentdopant may be used

Examples of the host include Alq₃, 4,4′-N,N′-dicarbazole-biphenyl (CBP),poly(n-vinylcarbazole) (PVK), 9,10-di(naphthylene-2-yl)anthracene (ADN),TCTA, 1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene (TPBI),3-tert-butyl-9,10-di(naphth-2-yl)anthracene (TBADN), E3, distyrylarylene(DSA), dmCBP (see Formula below), and Compounds 501 to 509 below, butthe host is not limited thereto.

In some embodiments, an anthracene-based compound represented by Formula400 below may be used as the host.

In Formula 400, Ar₁₁₁ and Ar₁₁₂ may each independently be a substitutedor unsubstituted C₅-C₆₀ arylene group. Ar₁₁₃ to Ar₁₁₆ may eachindependently be a substituted or unsubstituted C₁-C₁₀ alkyl group or asubstituted or unsubstituted C₅-C₆₀ aryl group. g, h, i and j may eachindependently be an integer from 0 to 4.

For example, Ar₁₁₁ and Ar₁₁₂ in Formula 400 may each independently be aphenylene group, a naphthalene group, a phenanthrenylene group, or apyrenylene group; or

a phenylene group, a naphthalene group, a phenanthrenylene group, or apyrenylene group substituted with at least one of a phenyl group, anaphthyl group, or an anthryl group. However, Ar₁₁₁ and Ar₁₁₂ are notlimited thereto.

g, h, i, and j in Formula 400 may each independently be 0, 1, or 2.

Ar₁₁₃ to Ar₁₁₆ in Formula 400 may each independently be:

i) a C₁-C₁₀ alkyl group substituted with at least one of a phenyl group,a naphthyl group, or an anthryl group; or

ii) a phenyl group, a naphthyl group, an anthryl group, a pyrenyl group,a phenanthrenyl group, or a fluorenyl group; or

iii) a phenyl group, a naphthyl group, an anthryl group, a pyrenylgroup, a phenanthrenyl group, or a fluorenyl group substituted with atleast one of a deuterium atom, a halogen atom, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazine, ahydrazone, a carboxyl group or a salt thereof, a sulfonic acid group ora salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀alkoxy group, a phenyl group, a naphthyl group, an anthryl group, apyrenyl group, a phenanthrenyl group, or a fluorenyl group; or

However, Ar₁₁₃ to Ar₁₁₆ are not limited thereto.

For example, the anthracene-based compound represented by Formula 400above may be one of the following compounds, but is not limited thereto:

In some embodiments, an anthracene-based compound represented by Formula401 below may be used as the host:

Ar₁₂₂ to Ar₁₂₅ in Formula 401 are the same as Ar₁₁₃ in Formula 400, andthus detailed descriptions thereof will not be repeated here.

Ar₁₂₆ and Ar₁₂₇ in Formula 401 may each independently be a C₁-C₁₀ alkylgroup (e.g., a methyl group, an ethyl group, or a propyl group).

k and l in Formula 401 may each independently be an integer of 0 to 4.For example, k and l may be 0, 1, or 2.

In some embodiments, the anthracene-based compound represented byFormula 401 may be one of the following compounds, but is not limitedthereto:

When the OLED is a full color OLED, the EML may be patterned into a redEML, a green EML, and a blue EML.

At least one of the red EML, the green EML, and the blue EML may includeone of the following dopants below (ppy=phenylpyridine).

Examples of the blue dopant include the following compounds, but are notlimited thereto.

Examples of the red dopant include the following compounds, but are notlimited thereto:

Examples of the green dopant include the following compounds, but arenot limited thereto:

Examples of dopants that may be used in the EML include Pd-complexes orPt-complexes represented by the below Formulas, but are not limitedthereto:

Examples of dopants that may be used in the EML include Os-complexesrepresented by the below Formulas, but are not limited thereto:

When the EML includes a host and a dopant, the amount of the dopant maybe about 0.01 to about 15 parts by weight based on 100 parts by weightof the host, but the amount of the dopant is not limited thereto.

A thickness of the EML may be about 100 Å to about 1,000 Å, for example,about 200 Å to about 600 Å. When the thickness of the EML is withinthese ranges, the EML may have good light-emitting ability without asubstantial increase in driving voltage.

Then, an ETL may be formed on the EML by vacuum deposition, spincoating, casting, or the like. When the ETL is formed using vacuumdeposition or spin coating, the deposition or coating conditions may besimilar to those described above for the formation of the HIL, althoughthe deposition or coating conditions may vary depending on the compoundused to form the ETL.

A material for forming the ETL may be any material that can stablytransport electrons injected from an electron-injecting electrode(cathode). Examples of the materials for forming the ETL include aquinoline derivative such as tris(8-quinolinorate)aluminum (Alq₃), TAZ,BAlq, beryllium bis(benzoquinolin-10-olate (Bebq₂),9,10-di(naphthalene-2-yl)anthracene ADN, Compound 201, and Compound 202,but the material for forming the ETL is not limited thereto:

A thickness of the ETL may be about 100 Å to about 1,000 Å, for example,about 150 Å to about 500 Å. When the thickness of the ETL is withinthese ranges, the ETL may have satisfactory electron transportingability without a substantial increase in driving voltage.

In some embodiments, the ETL may further include a metal-containingmaterial in addition to the electron transporting organic compound.

The metal-containing material may include a lithium (Li) complex.Non-limiting examples of the Li complex include lithium quinolate (LiQ)and Compound 203 below:

Then, an EIL, which facilitates injection of electrons from the cathode,may be formed on the ETL. Any suitable electron-injecting material maybe used to form the EIL.

Examples of materials for forming the EIL include LiF, NaCl, CsF, Li₂O,and BaO. The deposition conditions of the EIL may be similar to thosedescribed above for the formation of the HIL, although the conditionsmay vary depending on the material used to form the EIL.

A thickness of the EIL may be about 1 Å to about 100 Å, for example,about 3 Å to about 90 Å. When the thickness of the EIL is within theseranges, the EIL may have satisfactory electron injection ability withouta substantial increase in driving voltage.

A second electrode is disposed on the organic layer. The secondelectrode may be a cathode, which is an electron injection electrode. Amaterial for forming the second electrode may be a metal, an alloy, oran electro-conductive compound (which are materials having low workfunctions), or a mixture thereof. For example, the second electrode maybe formed of lithium (Li), magnesium (Mg), aluminum (Al),aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In),magnesium-silver (Mg—Ag), or the like, and may be formed as a thin filmtype transmission electrode. In some embodiments, to manufacture atop-emission light-emitting diode, the transmission electrode may beformed of indium tin oxide (ITO) or indium zinc oxide (IZO).

Although the OLED according to embodiments of the present invention hasbeen described with reference to FIG. 1, the OLED is not limited to thestructure illustrated in FIG. 1.

In addition, when the EML is formed using a phosphorescent dopant, toprevent diffusion of triplet excitons or holes toward the ETL, a holeblocking layer (HBL) may be formed between the ETL and the EML orbetween the E-functional layer and the EML by, for example, vacuumdeposition, spin coating, casting, LB, or the like. When the HBL isformed using vacuum deposition or spin coating, the deposition orcoating conditions may be similar to those described above for theformation of the HIL, although the conditions for deposition or coatingmay vary depending on the material used to form the HBL. Anyhole-blocking material may be used. Examples of hole-blocking materialsinclude oxadiazole derivatives, triazole derivatives, and phenanthrolinederivatives. For example, BCP (illustrated below) may be used as thematerial for the HBL.

A thickness of the HBL may be about 20 Å to about 1,000 Å, for example,about 30 Å to about 300 Å. When the thickness of the HBL is within theseranges, the HBL may have improved hole blocking ability without asubstantial increase in driving voltage.

The OLED according to an embodiment of the present invention may beprovided in various types of flat panel display devices, such as passivematrix OLED devices and active matrix OLED devices. In particular, whenthe OLED is provided in an active matrix OLED, the first electrode onthe substrate, which acts as a pixel electrode, may be electricallyconnected to a source electrode or a drain electrode of a thin-filmtransistor (TFT). In addition, the OLED may be provided in a flat paneldisplay device having double-sided screens.

In some embodiments, the organic layer of the organic light-emittingdevice (which includes the compound of Formula 1) may be formed bydeposition or by a wet process including coating a solution of thecompound of Formula 1.

Hereinafter, the present invention will be described with reference tothe following synthesis examples and other examples. However, theseexamples are presented for illustrative purposes only and are notintended to limit the scope of the present invention.

EXAMPLE Synthesis Example 1 Synthesis of Compound 1

Synthesis of Intermediate I-1

After dissolving 10.0 g (55.4 mmol) of 9,10-dihydro-phenanthrene, 21.8 g(121.0 mmol) of N-bromosuccinimide, and 0.5 g (2.7 mmol) of p-TsOH in 30mL of acetonitrile, the reaction solution was stirred at a temperatureof about 50° C. for about 12 hours. The reaction solution was cooled toroom temperature, and then stirred for about 30 minutes to precipitatecrystals. The crystals obtained by a vacuum filter were washed withmethanol to obtain 8.4 g of Intermediate I-1 (Yield: 45%) which was grayin color. The obtained compound was identified by LC-MS (C₁₄H₁₀Br₂ M⁺336.9).

Synthesis of Intermediate I-2

After completely dissolving 5.0 g of Intermediate I-1 (15.0 mmol) in 50mL of dichloromethane, 1.7 g of nitric acid (30.0 mmol) was addedthereto at room temperature. Then, 1.5 g of sulfuric acid (15.0 mmol)was slowly added thereto, and then the reaction solution was stirred ata temperature of about 30° C. for about 6 hours. After completion of thereaction, the reaction solution was cooled to room temperature, 50 mL ofmethanol was added thereto, and the solution was then stirred for about2 hours to precipitate crystals. The crystals obtained by a vacuumfilter were washed with methanol to obtain 5.2 g of Intermediate I-2(Yield: 90%) which was yellow in color. The obtained compound wasidentified by LC-MS (C₁₄H₉Br₂NO₂ M⁺ 381.9).

Synthesis of Intermediate I-3

After completely dissolving 4.6 g of Intermediate I-2 (12.0 mmol) in 30mL of o-dichlorobenzene and heating the reaction solution, 4.7 g oftriphenylphosphine (18.0 mmol) was added thereto. Then, the reactionsolution was stirred at a temperature of about 180° C. for about 3hours. After the reaction solution was cooled to room temperature,solvent was evaporated and the residue was separation-purified by silicagel column chromatography and then washed with methanol to obtain 2.9 gof Intermediate I-3 (Yield: 70%) which was white in color. The obtainedcompound was identified by LC-MS (C₁₄H₉Br₂N M⁺ 349.9)

Synthesis of Intermediate I-4

After dissolving 10 g of Intermediate I-3 (28.5 mmol) and 0.03 g of Pd/C(10%) (0.28 mmol) in 100 mL of ethanol, the temperature of the reactionsolution was increased to 50° C. 5.48 g of hydrazine (171 mmol) wasadded thereto, and the solution was then stirred for about 24 hours. Thereaction solution was cooled to room temperature, and washed withacetone. Then, 100 mL of ice water was added thereto to obtain 3.63 g ofIntermediate I-4 (Yield: 66%) which was white in color. The obtainedcompound was identified by LC-MS (C₁₄H₁₁N M+ 194.1).

Synthesis of Intermediate I-5

After dissolving 1.93 g of Intermediate I-4 (10.0 mmol), 2.5 g ofiodobenzene (12.0 mmol), 0.2 g of 1,10-phenanthroline (1.0 mmol), 0.2 gof CuI (2.0 mmol), and 4.1 g of K₂CO₃ (30.0 mmol) in 30 mL ofN,N-dimethylformamide (DMF), the reaction solution was stirred at atemperature of about 80° C. for about 24 hours. The reaction solutionwas cooled to room temperature, and then extracted three times with 30mL of water and 40 mL of diethyl ether. The organic layer obtainedtherefrom was dried with magnesium sulfate, solvent was evaporated, andthe residue was separation-purified by silica gel column chromatographyto obtain 2.39 g of Intermediate I-5 (Yield: 89%). The obtained compoundwas identified by LC-MS (C₂₀H₁₅N M⁺ 270.1).

Synthesis of Intermediate I-6

After completely dissolving 10 g of Intermediate I-5 (37.1 mmol) in 100ml of dichloromethane, 3.58 g of iodine (14.1 mmol) and 2.38 g of KIO₃(11.13 mmol) were added thereto in a 1/5 split. The reaction solutionwas stirred for about 6 hours and then washed with methanol to obtain8.06 g of Intermediate I-6 (Yield: 55%). The obtained compound wasidentified by LC-MS (C₂₀H₁₄IN M+ 396.1).

Synthesis of Intermediate I-7

After dissolving 10 g of Intermediate I-6 (25.3 mmol) in 100 ml oftoluene in an oxygen atmosphere, 1.57 g of2,3-dichloro-5,6-dicyano-1,4-benzoquinone (7.6 mmol) and 0.52 g of NaNO₂(7.6 mmol) were added thereto at room temperature. The reaction solutionwas stirred at a temperature of about 110° C. for about 6 hours, andafter cooling the reaction solution to room temperature, the solvent wasevaporated and the residue was separation-purified by silica gel columnchromatography to obtain 8.94 g of Intermediate I-7 (Yield: 90%). Theobtained compound was identified by LC-MS (C₂₀H₁₂IN M+ 394.0)

Synthesis of Intermediate 2-1

After dissolving 3.24 g of 4-bromo-N,N-diphenylaniline (10 mmol), 2.310g of vinyl-boronic acid pinacol-ester (15 mmol), 0.577 g of Pd(PPh₃)₄(0.5 mmol), and 1.658 g of K₂CO₃ (12 mmol) in 100 mL of THF/H₂O (2/1volume ratio), the reaction solution was stirred at a temperature ofabout 80° C. for about 5 hours. The reaction solution was cooled to roomtemperature, and then extracted three times with 40 mL of water and 50mL of ethyl ether. The organic layer obtained therefrom was dried withmagnesium sulfate, the solvent was evaporated, and the residue wasseparation-purified by silica gel column chromatography to obtain 1.6 gof Intermediate 2-1 (Yield: 59%). The obtained compound was identifiedby LC-MS (C₂₀H₁₇N M+ 272.1).

Synthesis of Compound 1

After dissolving 3.93 g of Intermediate I-7 (10 mmol), 2.71 g ofIntermediate 2-1 (10 mmol), 0.11 g of Pd(OAc)₂ (0.5 mmol), 0.15 g of(p-toly)₃P (0.5 mmol), and 1.01 g of Et₃N (10 mmol) in 50 mL of dimethylacetamide (DMAc), the reaction solution was stirred at a temperature ofabout 85° C. for about 4 hours. The reaction solution was cooled to roomtemperature, and then extracted three times with 100 mL of water and 100mL of ethyl ether. The organic layer obtained therefrom was dried withmagnesium sulfate, the solvent was evaporated, and the residue wasseparation-purified by silica gel column chromatography to obtain 3.53 gof Compound 1 (Yield: 66%). The obtained compound was identified byMS/FAB and ¹H NMR.

Synthesis Example 2 Synthesis of Compound 13

Synthesis of Intermediate I-8

3.89 g (Yield: 61%) of Intermediate I-8 was synthesized in the samemanner as the synthesis of Compound 1 using Intermediate I-7 andIntermediate 2-13(N-(naphthalene-2-yl)-N-phenyl-6-vinylnaphthalene-2-amine). The obtainedcompound was identified by LC-MS (C₄₈H₃₂N₂ M+ 637.3).

Synthesis of Compound 13

After dissolving 0.76 g (1.2 mmol) of Intermediate I-8, 0.081 g (0.08mmol) of [(Ph₃)P]₃Ru(CO)(Cl)H (carbonyl-chlororo-hydrido-tris(triphenylphosphine) ruthenium (II)), and 0.56 g (28.0 mmol) of D₂O in30 mL of 1,4-dioxane, the reaction solution was stirred at a temperatureof about 80 t for about 12 hours. The reaction solution was cooled toroom temperature, and then extracted three times with 50 mL of water and50 mL of dichloromethane. The organic layer obtained therefrom was driedwith magnesium sulfate, the solvent was evaporated, and the residue wasseparation-purified by silica gel column chromatography to obtain 0.71 gof Compound 13 (Yield: 94%). The obtained compound was identified byMS/FAB and ¹H NMR.

Synthesis Example 3 Synthesis of Compound 21

4.69 g of Compound 21 (Yield: 60%) was synthesized in the same manner asthe synthesis of Compound 1 using Intermediate I-7 and Intermediate2-21. The obtained compound was identified by MS/FAB and ¹H NMR.

Synthesis Example 4 Synthesis of Compound 25

Synthesis of Intermediate I-9

4.54 g (Yield: 66%) of Intermediate I-9 was synthesized in the samemanner as the synthesis Compound 1 using Intermediate I-7 andIntermediate 2-25. The obtained compound was identified by LC-MS(C₄₉H₃₄F₂N₂ M+ 687.3).

Synthesis of Compound 25

0.75 g (Yield: 90%) of Compound 25 was synthesized in the same manner asthe synthesis of Compound 13 using Intermediate I-9. The obtainedcompound was identified by MS/FAB and ¹H NMR.

Synthesis Example 5 Synthesis of Compound 35

6.01 g (Yield: 70%) of Compound 35 was synthesized in the same manner asthe synthesis of Compound 1 using Intermediate I-7 and Intermediate2-35. The obtained compound was identified by MS/FAB and ¹H NMR.

Synthesis Example 6 Synthesis of Compound 41

5.48 g of (Yield: 68%) of Compound 41 was synthesized in the same manneras the synthesis of Compound 1 using Intermediate I-7 and Intermediate2-41. The obtained compound was identified by MS/FAB and ¹H NMR.

Synthesis Example 7 Synthesis of Compound 49

Synthesis of Intermediate 3-1

3.18 g (Yield: 75%) of Intermediate 3-1 was synthesized in the samemanner as the synthesis of Intermediate 2-1 using Intermediate I-7 and4-bromophenyl-boronic acid. The obtained compound was identified byLC-MS (C₂₆H₁₈BrN M+ 424.1).

Synthesis of Compound 49

3.98 g (Yield: 65%) of Compound 49 was synthesized in the same manner asthe synthesis of Compound 1 using Intermediate 2-1 and Intermediate 3-1.The obtained compound was identified by MS/FAB and ¹H NMR.

Synthesis Example 8 Synthesis of Compound 52

6.14 g (Yield: 72%) of Compound 52 was synthesized in the same manner asthe synthesis of Compound 49 using Intermediate 3-1 and Intermediate2-52. The obtained compound was identified by MS/FAB and ¹H NMR.

Synthesis Example 9 Synthesis of Compound 57

5.15 g (Yield: 67%) of Compound 57 was synthesized in the same manner asthe synthesis of Compound 49 using Intermediate 3-2 and Intermediate2-57. The obtained compound was identified by MS/FAB and ¹H NMR.

Synthesis Example 10 Synthesis of Compound 61

5.46 g (Yield: 75%) of Compound 61 was synthesized in the same manner asthe synthesis of Compound 49 using Intermediate 3-3 and Intermediate2-1. The obtained compound was identified by MS/FAB and ¹H NMR.

Synthesis Example 11 Synthesis of Compound 67

5.48 g (Yield: 77%) of Compound 67 was synthesized in the same manner asthe synthesis of Compound 49 using Intermediate 3-4 and Intermediate2-67. The obtained compound was identified by MS/FAB and ¹H NMR.

Synthesis Example 12 Synthesis of Compound 71

4.20 g (Yield: 63%) of Compound 71 was synthesized in the same manner asthe synthesis of Compound 49 using Intermediate 3-5 and Intermediate2-71. The obtained compound was identified by MS/FAB and ¹H NMR.

Synthesis Example 13 Synthesis of Compound 73

Synthesis of Intermediate I-10

After completely dissolving 1.91 g (10.0 mmol) of 6H-benzo[def]carbazolein 60 mL of carbon tetrachloride (CCl₄), 1.78 g (10.0 mmol) ofN-bromosuccinimide was added thereto, and the reaction solution wasstirred at a temperature of about 80° C. for about 30 minutes. Thereaction solution was cooled to room temperature, and then stirred forabout 30 minutes to precipitate crystals. The crystals obtained by avacuum filter were washed with methanol to obtain 1.22 g (Yield: 45%) ofIntermediate I-10 which was white in color. The obtained compound wasidentified by LC-MS (C₁₄H₈BrN M⁺ 269.9).

Synthesis of Intermediate I-11

Intermediate I-11 was synthesized in the same manner as the synthesis ofIntermediate I-5, except Intermediate I-10 was used instead ofIntermediate I-4. The obtained compound was identified by LC-MS(C₂₀H₁₂BrN M⁺ 346.0).

Synthesis of Compound 73

3.86 g (Yield: 72%) of Compound 73 was synthesized in the same manner asthe synthesis of Compound 1 using Intermediate 2-1 and IntermediateI-11. The obtained compound was identified by MS/FAB and ¹H NMR.

Synthesis Example 14 Synthesis of Compound 75

4.83 g (Yield: 74%) of Compound 75 was synthesized in the same manner asthe synthesis of Compound 73 using Intermediate I-11 and Intermediate2-75. The obtained compound was identified by MS/FAB and ¹H NMR.

Synthesis Example 15 Synthesis of Compound 84

4.34 g (Yield: 69%) of Compound 84 was synthesized in the same manner asthe synthesis of Compound 73 using Intermediate I-11 and Intermediate2-84. The obtained compound was identified by MS/FAB and ¹H NMR.

Synthesis Example 16 Synthesis of Compound 85

0.69 g (Yield: 91%) of Compound 85 was synthesized in the same manner asthe synthesis of Compound 13 using Intermediate I-11 and Intermediate2-13. The obtained compound was identified by MS/FAB and ¹H NMR.

Synthesis Example 17 Synthesis of Compound 90

5.48 g (Yield: 73%) of Compound 90 was synthesized in the same manner asthe synthesis of Compound 73 using Intermediate I-11 and Intermediate2-90. The obtained compound was identified by MS/FAB and ¹H NMR.

Synthesis Example 18 Synthesis of Compound 92

5.29 g (Yield: 70%) of Compound 92 was synthesized in the same manner asthe synthesis of Compound 73 using Intermediate I-11 and Intermediate2-21. The obtained compound was identified by MS/FAB and ¹H NMR.

Synthesis Example 19 Synthesis of Compound 93

5.09 g (Yield: 78%) of Compound 93 was synthesized in the same manner asthe synthesis of Compound 73 using Intermediate I-11 and Intermediate2-93. The obtained compound was identified by MS/FAB and ¹H NMR.

Synthesis Example 20 Synthesis of Compound 103

5.26 g (Yield: 66%) of Compound 103 was synthesized in the same manneras the synthesis of Compound 73 using Intermediate I-11 and Intermediate2-103. The obtained compound was identified by MS/FAB and ¹H NMR.

Synthesis Example 21 Synthesis of Compound 104

0.68 g (Yield: 88%) of Compound 104 was synthesized in the same manneras the synthesis of Compound 85 using Intermediate I-11 and Intermediate2-104. The obtained compound was identified by MS/FAB and ¹H NMR.

Synthesis Example 22 Synthesis of Compound 110

4.77 g (Yield: 75%) of Compound 110 was synthesized in the same manneras the synthesis of Compound 73 using Intermediate I-11 and Intermediate2-110. The obtained compound was identified by MS/FAB and ¹H NMR.

Synthesis Example 23 Synthesis of Compound 115

4.84 g (Yield: 79%) of Compound 115 was synthesized in the same manneras the synthesis of Compound 73 using Intermediate 3-6 and Intermediate2-1. The obtained compound was identified by MS/FAB and ¹H NMR.

Synthesis Example 24 Synthesis of Compound 118

6.05 g (Yield: 71%) of Compound 118 was synthesized in the same manneras the synthesis of Compound 73 using Intermediate 3-6 and Intermediate2-52. The obtained compound was identified by MS/FAB and ¹H NMR.

Synthesis Example 25 Synthesis of Compound 122

4.95 g (Yield: 68%) of Compound 122 was synthesized in the same manneras the synthesis of Compound 73 using Intermediate 3-6 and Intermediate2-93. The obtained compound was identified by MS/FAB and ¹H NMR.

Synthesis Example 26 Synthesis of Compound 124

5.37 g (Yield: 66%) of Compound 124 was synthesized in the same manneras the synthesis of Compound 73 using Intermediate 3-7 and Intermediate2-1. The obtained compound was identified by MS/FAB and ¹H NMR.

Synthesis Example 27 Synthesis of Compound 129

4.59 g (Yield: 63%) of Compound 129 was synthesized in the same manneras the synthesis of Compound 73 using Intermediate 3-8 and Intermediate2-1. The obtained compound was identified by MS/FAB and ¹H NMR.

Synthesis Example 28 Synthesis of Compound 133

5.83 g (Yield: 70%) of Compound 133 was synthesized in the same manneras the synthesis of Compound 73 using Intermediate 3-6 and Intermediate2-133. The obtained compound was identified by MS/FAB and ¹H NMR.

Synthesis Example 29 Synthesis of Compound 135

4.15 g (Yield: 60%) of Compound 135 was synthesized in the same manneras the synthesis of Compound 73 using Intermediate 3-9 and Intermediate2-135. The obtained compound was identified by MS/FAB and ¹H NMR.

Synthesis Example 30 Synthesis of Compound 136

0.83 g (Yield: 89%) of Compound 136 was synthesized in the same manneras the synthesis of Compound 85 using Intermediate 3-10 and Intermediate2-104. The obtained compound was identified by MS/FAB and ¹H NMR.

Intermediates

The results of ¹H NMR and MS/FAB of the synthesized compounds are shownin Table 1 below.

TABLE 1 MS/FAB Comp. ¹H NMR (CDCl₃, 400 MHz) found calc. 1 δ = 7.77-7.76(m, 1H), 7.66 (s, 1H), 7.62-7.61 (m, 1H), 7.57-7.42 (m, 10H), 537.23536.23 7.38-7.36 (m, 2H), 7.31-7.27 (ss, 1H), 7.08-7.03 (m, 4H),6.70-6.62 (m, 4H), 6.16-6.13 (m, 4H) 13 δ = 7.91 (m, 1H), 7.78-7.64 (m,8H), 7.57-7.36 (m, 13H), 7.28 (d, 1H), 639.27 638.27 7.14 (dd, 1H),7.09-7.05 (m, 2H), 6.98-6.95 (m, 1H), 6.67-6.62 (m, 1H), 6.24-6.20 (m,2H) 21 δ = 7.77-7.69 (m, 4H), 7.65-7.61 (m, 5H), 7.59-7.49 (m, 12H),7.42-7.34 (m, 757.29 756.29 5H), 7.32 (s, 1H), 7.28-7.24 (m, 2H),7.06-7.02 (m, 3H), 6.96-6.92 (m, 1H), 6.46-6.44 (ss, 1H), 6.05-6.01 (m,2H) 25 δ = 7.78-7.75 (m, 1H), 7.68 (s, 1H), 7.66-7.64 (m, 2H), 7.62 (s,1H), 691.28 690.28 7.58-7.42 (m, 8H), 7.40-7.35 (m, 2H), 7.28 (d, 1H),7.15-7.07 (m, 2H), 7.01-6.93 (m, 4H), 6.69-6.66 (m, 2H), 6.61-6.59 (dd,1H), 6.47-6.46 (d, 1H), 1.61 (s, 6H) 35 δ = 8.05-8.04 (m, 1H), 8.00-7.98(m, 1H), 7.78-7.76 (m, 3H), 7.62 (m, 1H), 859.36 858.36 7.61 (ss, 2H),7.55-7.53 (m, 3H), 7.51-7.45 (m, 5H), 7.42-7.28 (m, 8H), 7.14-7.08 (m,4H), 7.00-6.95 (m, 2H), 6.90-6.89 (d, 1H), 6.88-6.87 (d, 1H), 6.53 (d,2H), 1.61 (s, 12H) 41 δ = 8.48-8.46 (m, 1H), 8.05-8.03 (ss, 1H), 7.97(m, 1H), 7.77-7.36 (m, 27H), 807.31 806.31 7.28 (d, 2H), 7.14-7.13 (d,1H), 7.10 (d, 1H), 7.06-7.04 (m, 1H), 6.77-6.74 (m, 1H), 6.63-6.60 (m,1H), 6.12-6.10 (m, 2H) 49 δ = 8.05 (d, 1H), 7.77-7.75 (m, 1H), 7.60-7.53(m, 5H), 7.50-7.38 (m, 9H), 613.26 612.26 7.31-7.30 (m, 2H), 7.26 (s,1H), 7.08-7.03 (m, 4H), 6.91-6.87 (ss, 1H), 6.70-6.63 (m, 4H), 6.16-6.13(m, 4H) 52 δ = 8.06 (m, 1H), 7.85-7.84 (m, 1H), 7.77-7.75 (m, 1H),7.60-7.53 (m, 6H), 853.35 852.35 7.51-7.45 (m, 8H), 7.40-7.38 (m, 2H),7.31 (m, 2H), 7.26 (s, 1H), 7.18-7.04 (m, 13H), 6.87-6.79 (m, 4H),6.66-6.63 (m, 1H), 6.46-6.43 (dd, 2H), 6.31-6.29 (m, 2H) 57 δ =8.93-8.91 (m, 1H), 8.61 (m, 1H), 8.50-8.49 (m, 1H), 8.19-8.17 (ss, 1H),770.26 769.26 8.13-8.11 (m, 2H), 7.91-7.81 (m, 4H), 7.77-7.75 (m, 1H),7.66-7.65 (ss, 2H), 7.57-7.54 (m, 2H), 7.48-7.33 (m, 10H), 7.20-7.16 (m,1H), 7.10-7.04 (m, 4H), 6.97-6.95 (m, 2H), 6.66-6.63 (m, 1H), 6.39-6.37(m, 2H) 61 δ = 8.03 (m, 1H), 7.81 (m, 1H), 7.77-7.75 (m, 1H), 7.74-7.71(ss, 1H), 729.32 728.32 7.66-7.64 (m, 2H), 7.62-7.60 (dd, 1H), 7.57-7.53(m, 3H), 7.47-7.35 (m, 9H), 7.32-7.30 (m, 1H), 7.24 (d, 1H), 7.08-7.03(m, 5H), 6.70-6.62 (m, 4H), 6.16-6.13 (m, 4H), 1.60 (s, 6H) 67 δ =8.93-8.91 (m, 1H), 8.15-8.13 (m, 2H), 8.03 (m, 1H), 7.86-7.84 (m, 1H),713.29 712.29 7.77 (ss, 1H), 7.72-7.70 (ss, 2H), 7.66-7.62 (m, 3H),7.57-7.53 (m, 3H), 7.50-7.38 (m, 7H), 7.32-7.30 (m, 1H), 7.21-7.18 (m,2H), 7.08-7.04 (m, 4H), 6.98-6.94 (m, 2H), 6.66-6.63 (m, 2H), 6.19-6.16(m, 4H) 71 δ = 9.00-8.99 (m, 1H), 8.19-8.15 (m, 2H), 8.12-8.10 (m, 2H),8.05-8.01 (m, 667.28 666.28 2H), 7.95-7.93 (dd, 1H), 7.88-7.86 (m, 1H),7.78-7.69 (m, 4H), 7.64-7.59 (m, 2H), 7.51-7.47 (t, 1H), 7.37-7.25 (m,10H) 73 δ = 8.17-8.15 (dd, 1H), 7.81-7.80 (ss, 1H), 7.70-7.68 (ss, 1H),7.55-7.35 (m, 537.23 536.23 12H), 7.20-7.16 (ss, 1H), 7.08-7.03 (m, 4H),6.76-6.73 (m, 2H), 6.66-6.63 (m, 2H), 6.16-6.13 (m, 4H) 75 δ = 8.17-8.15(m, 1H), 7.81-7.76 (m, 2H), 7.70-7.68 (ss, 1H), 7.62 (m, 1H), 653.29652.29 7.58-7.30 (m, 13H), 7.20-7.16 (ss, 1H), 7.11-7.04 (m, 4H),6.76-6.74 (m, 2H), 6.69-6.63 (m, 2H), 6.39-6.38 (d, 1H), 6.24-6.21 (m,2H), 1.61 (s, 6H) 84 δ = 8.17-8.13 (m, 2H), 8.03-8.02 (m, 1H), 7.81-7.79(m, 1H), 7.72-7.68 (t, 3H), 630.23 629.23 7.63-7.60 (m, 2H), 7.55-7.47(m, 7H), 7.45-7.43 (m, 2H), 7.40-7.35 (m, 3H), 6.97-6.89 (m, 3H),6.82-6.78 (m, 2H), 6.55-6.50 (m, 2H) 85 δ = 8.17-8.15 (d, 1H), 7.89 (m,1H), 7.82-7.64 (m, 8H), 7.57-7.35 (m, 13H), 639.27 638.27 7.14-7.05 (m,3H), 6.98-6.95 (tt, 1H), 6.67-6.63 (m, 1H), 6.24-6.20 (m, 2H) 90 δ =8.20-8.18 (m, 1H), 8.12-8.10 (m, 2H), 7.89-7.86 (m, 1H), 7.80-7.79 (m,752.30 751.30 1H), 7.66-7.60 (m, 1H), 7.55-7.44 (m, 12H), 7.38-7.26 (m,7H), 7.22-7.14 (m, 2H), 7.06-7.01 (m, 4H), 6.94-6.91 (m, 1H), 6.83-6.79(m, 2H), 6.65-6.61 (m, 1H), 6.13-6.11 (m, 2H) 92 δ = 8.20-8.18 (m, 1H),7.81-7.79 (m, 1H), 7.75-7.36 (m, 26H), 7.21-7.19 (d, 757.29 756.29 1H),7.06-7.01 (m, 3H), 6.96-6.92 (m, 1H), 6.62-6.58 (m, 2H), 6.04-6.01 (m,2H) 93 δ = 8.17-8.15 (m, 1H), 7.81-7.79 (d, 1H), 7.75-7.73 (ss, 1H),7.70-7.68 (ss, 653.29 652.29 1H), 7.66-7.64 (m, 2H), 7.55-7.36 (m, 11H),7.24-7.20 (ss, 1H), 7.09-7.04 (m, 4H), 6.67-6.63 (m, 3H), 6.46-6.45 (d,1H), 6.15-6.13 (m, 4H), 1.61 (s, 6H) 103 δ = 8.17-8.15 (dd, 1H),8.05-8.03 (ss, 1H), 7.83-7.80 (m, 2H), 7.72-7.69 (m, 797.29 796.29 3H),7.65-7.60 (m, 3H), 7.57-7.34 (m, 19H), 7.14-7.10 (dd, 1H), 7.07-7.01 (m,3H), 6.81-6.79 (dd, 1H), 6.63-6.60 (m, 1H), 6.26-6.22 (m, 2H) 104 δ =8.18-8.16 (m, 2H), 8.15 (s, 1H), 8.03-8.01 (d, 1H), 7.81-7.76 (m, 2H),645.23 644.23 7.70-7.68 (ss, 1H), 7.61-7.59 (dd, 1H), 7.53-7.35 (m 9H,7.12-7.04 (m, 5H), 6.94-6.91 (dd, 1H), 6.66-6.63 (m, 2H), 6.33-6.30 (m,3H) 110 δ = 8.21-8.19 (dd, 1H), 7.91-7.89 (m, 2H), 7.82-7.80 (ss, 1H),7.72 (s, 2H), 637.26 636.26 7.62-7.36 (m, 12H), 7.04-6.98 (m, 6H),6.88-6.84 (m, 2H), 6.63-6.60 (m, 2H), 5.97-5.94 (m, 4H) 115 δ = 7.77 (s,1H), 7.75-7.72 (m, 3H), 7.60-7.35 (m, 13H), 7.32-7.30 (m, 1H), 613.26612.26 7.13 (s, 1H), 7.09-7.03 (m, 4H), 6.91-6.87 (ss, 1H), 6.70-6.62(m, 4H), 6.16-6.13 (m, 4H) 118 δ = 7.85-7.84 (m, 1H), 7.77 (s, 1H),7.75-7.72 (m, 3H), 7.60-7.44 (m, 14H), 853.35 852.35 7.40-7.36 (m, 1H),7.32-7.30 (m, 1H), 7.18-7.16 (dd, 1H), 7.14-7.04 (m, 13H), 6.91 (s, 1H),6.84-6.79 (m, 3H), 6.66-6.63 (m, 1H), 6.46-6.43 (dd, 1H), 6.38-6.36 (dd,1H), 6.32-6.29 (m, 2H) 122 δ = 7.77 (s, 1H), 7.75-7.72 (m, 4H),7.68-7.66 (ss, 1H), 7.64 (m, 1H), 729.32 728.32 7.60-7.46 (m, 9H),7.44-7.30 (m, 4H), 7.09-7.04 (m, 6H), 6.67-6.62 (m, 3H), 6.46-6.45 (d,1H), 6.16-6.13 (m, 4H), 1.61 (s, 6H) 124 δ = 8.08-8.05 (m, 1H),8.00-7.98 (ss, 1H), 7.82-7.73 (m, 8H), 7.61-7.58 (ss, 815.33 814.33 1H),7.54-7.32 (m, 16H), 7.08-7.04 (m, 6H), 7.00-6.96 (m, 1H), 6.76-6.73 (m,2H), 6.66-6.62 (m, 2H), 6.16-6.13 (m, 4H) 129 δ = 7.95 (d, 1H),7.92-7.86 (m, 2H), 7.75-7.73 (m, 1H), 7.66-7.60 (m, 3H), 729.32 728.327.55-7.30 (m, 14H), 7.08-7.03 (m, 5H), 6.70-6.63 (m, 4H), 6.16-6.13 (m,4H), 1.64 (s, 6H) 133 δ = 8.08-8.05 (m, 1H), 7.95 (m, 1H), 7.77 (s, 1H),7.75-7.38 (m, 27H), 833.33 832.33 7.32-7.29 (m, 3H), 7.19 (s, 1H), 7.14(d, 1H), 7.10-7.03 (m, 3H), 6.63-6.60 (m, 1H), 6.12 (m, 2H) 135 δ = 8.89(d, 1H), 8.09-8.07 (dd, 1H), 7.83 (t, 1H), 7.80-7.76 (m, 4H), 692.30691.30 7.71-7.48 (m, 11H), 7.40-7.38 (m, 4H), 7.30-7.28 (m, 2H),7.13-7.04 (m, 4H), 6.72-6.63 (m, 3H), 6.24-6.22 (m, 2H), 1.29 (s, 3H)136 δ = 8.10-8.08 (m, 2H), 8.02-8.01 (m, 2H), 7.97-7.94 (m, 2H),7.89-7.87 (m, 771.27 770.27 2H), 7.78-7.73 (m, 2H), 7.60 (s, 1H),7.58-7.47 (m, 8H), 7.40-7.36 (m, 2H), 7.32-7.30 (dd, 1H), 7.12-7.04 (m,5H), 6.94-6.91 (dd, 1H), 6.66-6.63 (m, 2H), 6.33-6.29 (m, 4H)

Example 1

An anode was prepared by cutting a Corning 15Ω/cm² (1,200 Å) ITO glasssubstrate to a size of 50 mm×50 mm×0.7 mm, sonicating the cut substratein isopropyl alcohol for about 5 minutes and in pure water for about 5minutes, and then cleaning the substrate by irradiation of ultravioletrays for about 30 minutes, and exposing the substrate to ozone.

2-TNATA was vacuum deposited on the anode to a thickness of about 600 Åto form an HIL, and 4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl(hereinafter, NPB) as a hole transporting compound was vacuum-depositedon the HIL to a thickness of about 300 Å.

9,10-di-naphthalene-2-yl-anthracene (hereinafter, DNA) as a bluefluorescent host, and Compound 1 as a blue fluorescent dopant, wereco-deposited at a weight ratio of about 98:2 on the HTL to form an EMLhaving a thickness of 300 Å.

Next, Alq₃ was deposited on the EML to form an ETL having a thickness ofabout 300 Å, and then LiF, which is a halogenated alkali metal, wasdeposited on the ETL to form an EIL having a thickness of about 10 Å.Then, Al was vacuum-deposited on the EIL to form a cathode having athickness of about 3,000 Å, thereby forming a LiF/Al electrode andcompleting the manufacture of an OLED.

The OLED had a driving voltage of about 6.43 V at a current density of50 mA/cm², a luminosity of 2,280 cd/m², a luminescent efficiency of 4.56cd/A, and a half life-span (hr @100 mA/cm²) of about 217 hours.

Example 2

An OLED was manufactured as in Example 1, except that Compound 13 wasused instead of Compound 1 to form the EML.

The OLED had a driving voltage of about 6.43 V at a current density of50 mA/cm², a luminosity of 2,420 cd/m², a luminescent efficiency of 4.84cd/A, and a half life-span (hr @100 mA/cm²) of about 258 hours.

Example 3

An OLED was manufactured as in Example 1, except that Compound 25 wasused instead of Compound 1 to form the EML.

The OLED had a driving voltage of about 6.58 V at a current density of50 mA/cm², a luminosity of 2,705 cd/m², a luminescent efficiency of 5.41cd/A, and a half life-span (hr @100 mA/cm²) of about 236 hours.

Example 4

An OLED was manufactured as in Example 1, except that Compound 41 wasused instead of Compound 1 to form the EML.

The OLED had a driving voltage of about 6.45 V at a current density of50 mA/cm², a luminosity of 2,675 cd/m², a luminescent efficiency of 5.35cd/A, and a half life-span (hr @100 mA/cm²) of about 277 hours.

Example 5

An OLED was manufactured as in Example 1, except that Compound 49 wasused instead of Compound 1 to form the EML.

The OLED had a driving voltage of about 6.05 V at a current density of50 mA/cm², a luminosity of 2,885 cd/m², a luminescent efficiency of 5.77cd/A, and a half life-span (hr @100 mA/cm²) of about 296 hours.

Example 6

An OLED was manufactured as in Example 1, except that Compound 61 wasused instead of Compound 1 to form the EML.

The OLED had a driving voltage of about 6.24 V at a current density of50 mA/cm², a luminosity of 2,765 cd/m², a luminescent efficiency of 5.53cd/A, and a half life-span (hr @100 mA/cm²) of about 262 hours.

Example 7

An OLED was manufactured as in Example 1, except that Compound 71 wasused instead of Compound 1 to form the EML.

The OLED had a driving voltage of about 6.61 V at a current density of50 mA/cm², a luminosity of 2,530 cd/m², a luminescent efficiency of 5.06cd/A, and a half life-span (hr @100 mA/cm²) of about 243 hours.

Example 8

An OLED was manufactured as in Example 1, except that Compound 73 wasused instead of Compound 1 to form the EML.

The OLED had a driving voltage of about 6.31 V at a current density of50 mA/cm², a luminosity of 2,470 cd/m², a luminescent efficiency of 4.94cd/A, and a half life-span (hr @100 mA/cm²) of about 225 hours.

Example 9

An OLED was manufactured as in Example 1, except that Compound 84 wasused instead of Compound 1 to form the EML.

The OLED had a driving voltage of about 6.42 V at a current density of50 mA/cm², a luminosity of 2,555 cd/m², a luminescent efficiency of 5.11cd/A, and a half life-span (hr @100 mA/cm²) of about 242 hours.

Example 10

An OLED was manufactured as in Example 1, except that Compound 92 wasused instead of Compound 1 to form the EML.

The OLED had a driving voltage of about 6.34 V at a current density of50 mA/cm², a luminosity of 2,715 cd/m², a luminescent efficiency of 5.43cd/A, and a half life-span (hr @100 mA/cm²) of about 279 hours.

Example 11

An OLED was manufactured as in Example 1, except that Compound 104 wasused instead of Compound 1 to form the EML.

The OLED had a driving voltage of about 6.47 V at a current density of50 mA/cm², a luminosity of 2,525 cd/m², a luminescent efficiency of 5.05cd/A, and a half life-span (hr @100 mA/cm²) of about 257 hours.

Example 12

An OLED was manufactured as in Example 1, except that Compound 115 wasused instead of Compound 1 to form the EML.

The OLED had a driving voltage of about 6.08 V at a current density of50 mA/cm², a luminosity of 2,930 cd/m², a luminescent efficiency of 5.86cd/A, and a half life-span (hr @100 mA/cm²) of about 294 hours.

Example 13

An OLED was manufactured as in Example 1, except that Compound 122 wasused instead of Compound 1 to form the EML.

The OLED had a driving voltage of about 6.26 V at a current density of50 mA/cm², a luminosity of 2,860 cd/m², a luminescent efficiency of 5.72cd/A, and a half life-span (hr @100 mA/cm²) of about 277 hours.

Example 14

An OLED was manufactured as in Example 1, except that Compound 135 wasused instead of Compound 1 to form the EML.

The OLED had a driving voltage of about 6.41 V at a current density of50 mA/cm², a luminosity of 2,605 cd/m², a luminescent efficiency of 5.21cd/A, and a half life-span (hr @100 mA/cm²) of about 233 hours.

Comparative Example 1

An OLED was manufactured as in Example 1, except that the bluefluorescent dopant4,4′-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (hereinafter,referred as DPAVBi) was used instead of Compound 1 to form the EML.

The OLED had a driving voltage of about 7.35 V at a current density of50 mA/cm², a luminosity of 2,065 cd/m², a luminescent efficiency of 4.13cd/A, and a half life-span (hr @100 mA/cm²) of about 145 hours.

Compounds of Formula 1, according to embodiments of the presentinvention, were used as a blue dopant in the EML of the OLEDs ofExamples 1-14. Compared to the OLED using the blue fluorescent dopantDPVBi (i.e., Comparative Example 1), the OLEDs including the compoundsof Formula 1 showed improved driving voltage and I-V-L characteristicsas well as improved efficiency, and lifetime. The representativecharacteristics and lifetimes of the OLEDs of Examples 1-14 aresummarized in Table 2 below.

TABLE 2 Half-life Light- Driving Current lifetime emitting voltagedensity Brightness Efficiency Luminescence (hr @100 material (V)(mA/cm2) (cd/m2) (cd/A) color mA/cm²) Example 1 Compound 1 6.43 50 2,2804.56 Blue 217 hr Example 2 Compound 13 6.34 50 2,420 4.84 Blue 258 hrExample 3 Compound 25 6.58 50 2,705 5.41 Blue 236 hr Example 4 Compound41 6.45 50 2,675 5.35 Blue 277 hr Example 5 Compound 49 6.05 50 2,8855.77 Blue 296 hr Example 6 Compound 61 6.24 50 2,765 5.53 Blue 262 hrExample 7 Compound 71 6.61 50 2,530 5.06 Blue 243 hr Example 8 Compound73 6.31 50 2,470 4.94 Blue 225 hr Example 9 Compound 84 6.42 50 2,5555.11 Blue 242 hr Example 10 Compound 92 6.34 50 2,715 5.43 Blue 279 hrExample 11 Compound 104 6.47 50 2,525 5.05 Blue 257 hr Example 12Compound 115 6.08 50 2,930 5.86 Blue 294 hr Example 13 Compound 122 6.2650 2,860 5.72 Blue 277 hr Example 14 Compound 135 6.41 50 2,605 5.21Blue 233 hr

As described above, a heterocyclic compound represented by Formula 1 hasgood light-emitting ability, and thus may be effectively used as alight-emitting material suitable for fluorescent and phosphorescentdiodes emitting all colors, such as red green, blue, or white.Therefore, an organic electroluminescent device having high efficiency,low driving voltage, high luminance, and a long lifetime may bemanufactured using the compound.

While the present invention has been illustrated and described withreference to certain exemplary embodiments, it will be understood bythose of ordinary skill in the art that various changes may be made tothe described embodiments without departing from the spirit and scope ofthe present invention as defined by the following claims.

What is claimed is:
 1. A heterocyclic compound represented by Formula 1:

wherein, in Formula 1, A and B are each independently a single bond or abivalent linker that is a substituted or unsubstituted C₆-C₃₀ arylenegroup, a substituted or unsubstituted C₂-C₃₀ heteroarylene group, or asubstituted or unsubstituted C₆-C₃₀ condensed polycyclic group; R₁, R₂,and R₃ are each independently a hydrogen atom, a deuterium atom, asubstituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₃-C₆₀ cycloalkyl group, a substituted or unsubstitutedC₆-C₆₀ aryl group, a substituted or unsubstituted C₂-C₆₀ heteroarylgroup, a substituted or unsubstituted C₆-C₃₀ condensed polycyclic group,a fluoro group, or a cyano group; Ar₁ and Ar₂ are each independently asubstituted or unsubstituted C₆-C₃₀ aryl group, a substituted orunsubstituted C₂-C₃₀ heteroaryl group, or a substituted or unsubstitutedC₆-C₃₀ condensed polycyclic group; and Ar₁ and Ar₂ optionally combinewith each other or adjacent substituents to form a ring.
 2. Theheterocyclic compound of claim 1, wherein the heterocyclic compound isrepresented by Formula 2:


3. The heterocyclic compound of claim 1, wherein the heterocycliccompound is represented by Formula 3:


4. The heterocyclic compound of claim 1, wherein Ar₁ and Ar₂ combinewith each other or adjacent substituents to form a ring.
 5. Theheterocyclic compound of claim 1, wherein R₁ is a substituted orunsubstituted C₁-C₃₀ alkyl group, or a group represented by Formula 2aor Formula 2b:

wherein, in Formulas 2a and 2b, Z₁ is a hydrogen atom, a deuterium atom,a halogen atom, —CN, a substituted or unsubstituted C₁-C₂₀ alkyl group,a substituted or unsubstituted C₆-C₂₀ aryl group, or a substituted orunsubstituted C₂-C₂₀ heteroaryl group; Y₁ is CH or N; p is an integerfrom 1 to 6; and * is a binding site.
 6. The heterocyclic compound ofclaim 1, wherein R₂ and R₃ are each independently a hydrogen atom, adeuterium atom, a substituted or unsubstituted C₁-C₃₀ alkyl group, or agroup represented by Formula 3a:

wherein, in Formula 3a, Z₁ is a hydrogen atom, a deuterium atom, ahalogen atom, —CN, a substituted or unsubstituted C₁-C₂₀ alkyl group, asubstituted or unsubstituted C₆-C₂₀ aryl group, or a substituted orunsubstituted C₂-C₂₀ heteroaryl group; p is an integer from 1 to 5;and * is a binding site.
 7. The heterocyclic compound of claim 1,wherein Ar₁ and Ar₂ are each independently a group represented by one ofFormulas 4a to 4d:

wherein, in Formulas 4a to 4d, Z₁ is a hydrogen atom a deuterium atom, ahalogen atom, —CN, a substituted or unsubstituted C₁-C₂₀ alkyl group, asubstituted or unsubstituted C₆-C₂₀ aryl group, or a substituted orunsubstituted C₂-C₂₀ heteroaryl group; Y₁ is CH or N; Q₁ is a linkerrepresented by —C(R₃₀)(R₃₁)—, —S—, or —O—; R₃₀ and R₃₁ are eachindependently a hydrogen atom, a deuterium atom, a substituted orunsubstituted C₁-C₂₀ alkyl group, a substituted or unsubstituted C₆-C₂₀aryl group, or a substituted or unsubstituted C₆-C₂₀ condensedpolycyclic group; p is an integer from 1 to 9; and * is a binding site.8. The heterocyclic compound of claim 1, wherein A and B are eachindependently a single bond, a group represented by one of Formulas 5ato 5e, or a linker connecting at least two groups represented byFormulas 5a to 5e:

wherein, in Formulas 5a to 5e, Y₁ is CH or N; Q₂ is a linker representedby —C(R₃₀)(R₃₁)—, —S—, or —O—; R₃₀ and R₃₁ are each independently ahydrogen atom, a deuterium atom, a substituted or unsubstituted C₁-C₂₀alkyl group, a substituted or unsubstituted C₆-C₂₀ aryl group, or asubstituted or unsubstituted C₆-C₂₀ condensed polycyclic group; and * isa binding site.
 9. The heterocyclic compound of claim 1, wherein thecompound of Formula 1 is one of Compounds 1 through 137:


10. An organic light-emitting diode (OLED) comprising: a firstelectrode; a second electrode; and an organic layer between the firstelectrode and the second electrode, the organic layer comprising thecompound of claim
 1. 11. The OLED of claim 10, wherein the organic layeris an emission layer.
 12. The OLED of claim 10, wherein the organiclayer comprises an emission layer, and one or more of an electroninjection layer, an electron transport layer, a functional layer havingboth electron injection and electron transport capabilities, a holeinjection layer, a hole transport layer, or a functional layer havingboth hole injection and hole transport capabilities, wherein theemission layer comprises the compound represented by Formula 1, and theemission layer further comprises an anthracene-based compound, anarylamine-based compound, or a styryl-based compound.
 13. The OLED ofclaim 10, wherein the organic layer comprises an emission layer, and oneor more of an electron injection layer, an electron transport layer, afunctional layer having both electron injection and electron transportcapabilities, a hole injection layer, a hole transport layer, or afunctional layer having both hole injection and hole transportcapabilities, wherein the emission layer comprises the compoundrepresented by Formula 1, and one or more of a red emission layer, agreen emission layer, a blue emission layer, or a white emission layerof the emission layer comprises a phosphorescent compound.
 14. The OLEDof claim 13, wherein the hole injection layer, the hole transport layer,or the functional layer having both hole injection and hole transportcapabilities comprises a charge-generating material.
 15. The OLED ofclaim 14, wherein the charge-generating material is a p-dopant.
 16. TheOLED of claim 15, wherein the p-dopant is a quinone derivative, a metaloxide, or a cyano group-containing compound.
 17. The OLED of claim 10,wherein the organic layer comprises an electron transport layer, and theelectron transport layer comprises a metal complex.
 18. The OLED ofclaim 17, wherein the metal complex is a lithium (Li) complex.
 19. TheOLED of claim 10, wherein the organic layer comprising the compoundrepresented by Formula 1 is formed by a wet process.
 20. A flat paneldisplay device, comprising the OLED of claim 10, wherein the firstelectrode of the OLED is electrically connected to a source electrode ora drain electrode of a thin film transistor (TFT).